Bis(2-chloroethyl) ether → 4-(4-Chlorophenyl)tetrahydro-2H-pyran-4-carbonitrile

온도

0 °C

To a stirred suspension of 2-(4-chlorophenyl)acetonitrile (3.06 g, 20.3 mmol) at 0° C. in DMSO (200 mL) was added NaH (1.79 g, 60% in mineral oil, 44.6 mmol). The reaction was stirred at 0° C. for 15 min then at room temperature for 30 min, resulting in a dark purple solution. To this solution was added 1-chloro-2-(2-chloroethoxy)ethane (3.18 g, 22.33 mmol) dropwise. The resulting mixture was stirred at room temperature overnight before diluting with 50 mL water and neutralizing to pH˜7.0 with 1.0 M aq. HCl. The reaction was extracted with Et2O (3×200 mL) and the combined organics were washed with brine (200 mL), dried over Na2SO4, and concentrated. The residue was purified by flash chromatography on silica gel (10-30% EtOAc/hexane eluent) to provide 4-(4-chlorophenyl)tetrahydro-2H-pyran-4-carbonitrile as a yellow crystalline solid (4.01 g, 89% yield) (Note: This compound does not ionize well on LC/MS. It does not have intense UV absorption at 220 nM. The TLC Rf is 0.6 in 30% EA/Hexane).

1. waitat room temperature for 30 min
2. customresulting in a dark purple solution
3. stirringThe resulting mixture was stirred at room temperature overnight
4. extractionThe reaction was extracted with Et2O (3×200 mL)
5. washthe combined organics were washed with brine (200 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe residue was purified by flash chromatography on silica gel (10-30% EtOAc/hexane eluent)

ORD 기록

ord-0355844492594cfeb82e47c92e809d46

출처 데이터셋

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08440652B2